US4051130AExpiredUtility

4(3H)-oxobenzo-2,1,3-thiadiazine-2,2-dioxides and derivatives thereof

Assignee: DOW CHEMICAL COPriority: Aug 15, 1974Filed: Mar 12, 1976Granted: Sep 27, 1977

Est. expiryAug 15, 1994(expired)· nominal 20-yr term from priority

Inventors:Lennon H. Mckendry Walter P. Bland

C07D 285/16A01N 43/88A01N 47/16A01N 47/22A01N 47/38

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Claims

Abstract

Disclosed are novel 4(3H)-oxobenzo-2,1,3-thiadiazine-2,2-dioxides and derivatives and methods employing the same in the control of undesired vegetation.

Claims

exact text as granted — not AI-modified

What is claimed is: 
     
       1. A compound corresponding to the formula: ##STR28## wherein: each X independently represents loweralkyl, haloloweralkyl, cycloalkyl having from 3 to about 8 carbon atoms, phenyl, loweralkylphenyl, halophenyl, --SCN, --COOR 5 , ##STR29##  --YR 2 , --SO 2  R 5 , --SO 2  NR 3  R 4 , --CF 3 , ##STR30##  or --Y&#39;CF 2  C(Z) 3  ; n represents an integer of 1 to 4, inclusive; m represents an integer of 1 or 2;   R represents loweralkyl, haloloweralkyl; alkenyl, haloalkenyl, alkynyl and haloalkynyl, each of about 3 to about 6 carbon atoms; cycloalkyl of 3 to about 8 carbon atoms; phenyl, loweralkylphenyl, halophenyl, benzyl, loweralkylbenzyl, halobenzyl, loweralkoxyloweralkyl, diloweralkylaminoloweralkyl; loweralkylthioloweralkyl, or cyanoloweralkyl;   R 1  represents hydrogen, ##STR31##  --SO 2  R 10  or --SO 2  NR 8  R 9  ; R 2  and R 5  each represent alkyl of 1 to 2 carbon atoms;   R 3  represents loweralkyl;   R 4  represents hydrogen or loweralkyl;   R 6  represents loweralkyl and hololoweralkyl each having from 1 to 5 carbon atoms, alkenyl and haloalkenyl of 2 to 5 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, loweralkoxyloweralkyl and loweralkylthioloweralkyl, each of 2 to 6 carbon atoms, alkoxycarbonylalkyl of 4 to 8 carbon atoms, phenyl, loweralkylphenyl or halophenyl;   R 7  represents alkyl of 1 to 7 carbon atoms, haloalkyl of 1 to 4 carbon atoms, alkenyl and haloalkenyl of 3 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms, phenyl, loweralkylphenyl or halophenyl;   R 8  represents loweralkyl of 1 to 4 carbon atoms and cycloalkyl of 3 to 6 carbon atoms;   R 9  represents R 8  and alkoxy, and when taken together with R 8  and the nitrogen from which each depends, a heterocyclic ring of 4 to 8 carbon atoms;   R 10  represents alkyl and haloalkyl, each of 1 to 7 carbon atoms;   each Y, Y&#39; and Y&#34; independently represents a chalcogen group having an atomic number of from 8 to 16 inclusive;   each Z independently represents hydrogen, bromo, chloro or fluoro; and   where R 1  is hydrogen, the salts thereof with organic or inorganic bases.   
     
     
       2. The compound of claim 1 wherein m is 2. 
     
     
       3. The compound of claim 2 wherein R is loweralkyl. 
     
     
       4. The compound of claim 2 wherein R is loweralkyl and R 1  is hydrogen. 
     
     
       5. The compound of claim 2 wherein R is loweralkyl and R 1  is ##STR32## 
     
     
       6. The compound of claim 2 wherein R is loweralkyl and R 1  is --COY&#34;R 7 . 
     
     
       7. The compound of claim 2 wherein R is loweralkyl and R 1  is --SO 2  R 10 . 
     
     
       8. The compound of claim 1 wherein R is 1-methylethyl. 
     
     
       9. The compound of claim 3 wherein X is loweralkyl of from 1 to about 4 carbon atoms. 
     
     
       10. The compound of claim 9 wherein n is 1. 
     
     
       11. The compound of claim 3 wherein X is loweralkyl of from 1 to about 2 carbon atoms, n is 1, and R 1  is selected from hydrogen ##STR33## and --SO 2  R 10 . 
     
     
       12. The compound of claim 11 in which X is in one of the 6, 7 or 8 ring positions. 
     
     
       13. The compound of claim 2 which is 8-methyl-3-(n-propyl)-1H-2,1,3-benzothiadiazin-4-(3H)-one-2,2-dioxide. 
     
     
       14. The compound of claim 2 which is 8-methyl-3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide. 
     
     
       15. The compound of claim 2 which is 8-methyl-3-(sec. butyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide. 
     
     
       16. The compound of claim 2 which is 3,4-dihydro-8-methyl-3-(1-methylethyl)-4-oxo-1H-2,1,3-benzothiadiazine-1-carboxylic acid, methyl ester, 2,2-dioxide. 
     
     
       17. The compound of claim 2 which is 3,4-dihydro-8-methyl-3-(1-methylethyl)-4-oxo-1H-2,1,3-benzothiadiazine-1-carboxylic acid, propyl ester, 2,2-dioxide. 
     
     
       18. The compound of claim 2 which is 8-methyl-3-(1-methylethyl)-1-acetyl-11H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide. 
     
     
       19. The compound of claim 2 which is 8-methyl-3-(1-methylethyl)-1-(1-oxobutyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide. 
     
     
       20. The compound of claim 2 which is 3,4-dihydro-8-methyl-3-(1-methylethyl)-4-oxo-1H-2,1,3-benzothiadiazine-carboxylic acid, butyl ester, 2,2-dioxide. 
     
     
       21. The compound of claim 2 which is 8-methoxy-3-(1-methylethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide 
     
     
       22. The compound of claim 2 which is 3,4-dihydro-8-methyl-3-(1-methylethyl)-4-oxo-1H-2,1,3-benzothiadiazine-1-carbothioic acid, S-methyl ester, 2,2-dioxide. 
     
     
       23. The compound of claim 2 which is 3,4-dihydro-8-methyl-3-(1-methylethyl)-4-oxo-1H-2,1,3-benzothiadiazine-1-carbothioic acid, S-propyl ester, 2,2-dioxide. 
     
     
       24. The compound of claim 2 which is 8-methyl-3-(1-methylethyl)-1-methylsulfonyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide. 
     
     
       25. The compound of claim 2 which is 8-methyl-3-(1-methylethyl)-1-propylsulfonyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide. 
     
     
       26. The compound of claim 2 which is 8-methyl-3-(1-methylethyl)-1-butylsulfonyl-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide. 
     
     
       27. The compound of claim 1 which is 3-(1-methylethyl)-(8-trifluoromethyl)-1H-2,1,3-benzothiadiazin-4(3H)-one-2,2-dioxide.

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